Oxalyl hydrazide-hydroxamic acid derivatives, their preparation and their use as fungicides

ABSTRACT

Oxalyl hydrazide-hydroxamic acid derivatives of the formula I ##STR1## where the substituents have the following meanings: R, R 1 , R 2  and R 3  independently of one another are 
     hydrogen, substituted or unsubstituted alkyl, alkenyl or alkynyl or 
     substituted or unsubstituted cycloalkyl or cycloalkylmethyl, 
     substituted or unsubstituted cycloalkenyl or cycloalkenylmethyl, 
     substituted or unsubstituted phenyl, phenylalkyl, phenylalkenyl, hetaryl- or hetarylalkyl radicals, where R 2  and R 3  may also. together with the nitrogen atom whose substituents they are, form a 5- or 6-membered ring, or 
     R 2  together with R 3  is the group ##STR2## where R 4  and R 5  are one of the radicals R, R 1 , R 2  or R 3 , or R 4  together with R 5  and the carbon atom whose substituents they are, are monocyclic or polycyclic cycloalkyl, or 
     R 4  together with R 5  and the carbon atom whose substituents they are, form a 5- or 6-membered, saturated heterocycle containing O, S or --N(R 6 )-- as a hetero group, and fungicides containing these active ingredients.

The present invention relates to novel oxalyl hydrazide-hydroxamic acidderivatives of the general formula I ##STR3## where the substituentshave the following meanings: R, R¹, R², and R³ independently of oneanother are

hydrogen, C₁ -C₂₀ -alkyl, C₃ -C₁₈ -alkenyl or C₃ -C₈ -alkynyl, wherethese radicals can carry one to five halogen atoms or one to three C₁-C₄ -alkoxy groups, if appropriate together with the halogen atoms;

monocyclic or polycyclic C₃ -C₁₀ -cycloalkyl or C₃ -C₁₀-cycloalkylmethyl, where these rings can carry one to three C₁ -C₄-alkyl groups or a cyclohexyl ring;

monocyclic or polycyclic C₅ -C₁₀ -cycloalkenyl or C₅ -C₁₀-cycloalkenylmethyl, where these rings can carry one to three C₁ -C₄-alkyl groups or a cyclohexyl ring;

phenyl, phenyl-C₁ -C₄ -alkyl, phenyl-C₂ -C₆ -alkenyl, mononuclearheteroaryl or heteroaryl-C₁ -C₄ -alkyl radicals, where the(hetero)aromatic radicals can carry one to five halogen atoms or one tothree of the following groups, if appropriate together with the halogenatoms: hydroxyl, nitro, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄-alkoxy, C₁ -C₄ -haloalkoxy, COOR, CONH₂ or amines, where R² and R³ canalso form, together with the nitrogen atom whose substituents they are,a 5- or 6-member ring which additionally can be interrupted by oxygen,or

R² together with R³ is the group ##STR4## where R⁴ and R⁵ are one of theradicals R, R¹, R² or R³ or R⁴, together with R⁵ and the C atom whosesubstituents they are, are monocyclic or polycyclic C₃ -C₁₀ -cycloalkyl,where these rings can carry one to three C₁ -C₄ -alkyl groups or aphenyl ring, or

R⁴, together with R⁵ and the C atom whose substituents they are, form a5- or 6-membered, saturated heterocycle containing O, S or --N(R⁶)-- asa hetero group, where R⁶ is a C₁ -C₆ -alkyl group, or with twonon-adjacent identical or different heteroatoms, which can be oxygen,sulfur or the group --N(R⁶), as a hetero group,

and compositions which contain these oxalyl hydrazidehydroxamic acidderivatives as active compounds, processes for their preparation andprocesses for the control of fungal attack on useful plants using thesecompounds.

It is an object of the present invention to provide novel compoundswhich have a high fungicidal activity and a good plant tolerability.

We have found that this object is achieved by the oxalylhydrazide-hydroxamic acid derivatives I defined at the beginning andprocesses for their preparation.

According to the invention, compositions which contain these oxalylderivatives as active compound and a process for the control ofphytopathogenic fungi in useful plant crops using these compounds areprovided.

Specifically, the radicals R¹ to R⁵ in formula I have the followingmeanings:

R, R¹, R² and R³ are identical or different and can be widely varied.

For example, they are hydrogen, straight-chain or branched C₁ - to C₂₀-alkyl, in particular C₁ - to C₁₆ -alkyl such as methyl, ethyl,n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, pentyl, hexyl,heptyl, octyl, nonyl, decyl, undecyl, tridecyl, tetradecyl, pentadecyl,hexadecyl, heptadecyl, octadecyl and nonadecyl; straight-chain orbranched C₁ -C₂₀ -haloalkyl, in particular C₁ -C₁₂ -haloalkyl having 1to 5, for example 1 to 3, preferably 1 to 2 halogen atoms, such asiodine, bromine, in particular fluorine or chlorine, such aschlorobutyl, e.g. 1-chlorobutyl, 2-chlorobutyl, 3-chlorobutyl,4-chlorobutyl, 2,3-dichlorobutyl, chlorohexyl, e.g. 3-chlorohexyl,5-chlorohexyl, fluoropentyl, e.g. 3-fluoropentyl, fluorohexyl,fluoroheptyl, fluorodecyl, fluorododecyl; C₃ -C₁₈ -alkenyl, inparticular C₃ -C₁₆ -alkenyl having 1 to 3 double bonds in the alkenylradical, such as allyl, methallyl, pentenyl, hexenyl, heptenyl, octenyl,2-chloroallyl, 2-bromoallyl, 3-chloroallyl, 3-bromoallyl,2,3,3,-trichloroallyl, 3-chloro-2-butenyl, decenyl, dodecenyl, geranyl,hexadecenyl, octadecenyl; C.sub. 3 - or C₄ -alkynyl, such as propargylor 2-butinyl; unbridged or bridged, i.e. bearing 1 or 2 methylene orethylene bridges, C₃ -C₁₀ -cycloalkyl or C₃ -C₁₀ -cycloalkylmethyl, inparticular C₃ -C₈ -cycloalkyl or C₃ -C₈ -cycloalkylmethyl, it beingpossible for said cycloalkyl or cycloalkylalkyl radicals to be C₁ -C₅-alkyl-substituted or cyclohexyl-substituted. For example, the followingradicals may be mentioned, cycloalkyl radicals such as cyclopropyl,cyclopentyl, methylcyclopentyl, cyclohexyl, ethylcyclohexyl, propyl- andisopropylcyclohexyl, butyl-, iso-butyl-, sec-butyl- andtert-butylcyclohexyl, tert-amylcyclohexyl, cyclohexylcyclohexyl,cycloheptyl, methylcycloheptyl, propylcycloheptyl, cyclooctyl,cyclododecyl, decalyl (decahydronaphthyl); cycloalkylmethyl radicals,such as cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl,cyclododecylmethyl; bridged cycloalkyl or cycloalkylmethyl radicals suchas norbornyl, 1,5-dimethylbicyclo[2.3.1]octan-8-yl, tricyclodecanyl,norbornylmethyl, adamantyl and mono- and bicyclic terpene radicals suchas o-menthyl, m-menthyl, p-menthyl, bornyl, isobornyl, pinanyl,camphenyl and homocamphenyl.

The radicals R, R¹, R² and R³ are furthermore phenyl, phenyl-C₁ -C₄-alkyl, phenyl-C₂ -C₆ -alkenyl, mononuclear heteroaryl or heteroaryl-C₁-C₄ -alkyl radicals, which can be substituted by halogen, hydroxyl,nitro, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄-haloalkoxy, COOR, CONH₂ or amino groups, in particular phenyl,phenylmethyl, phenylethyl, phenylpropyl, 2-fluorophenyl, 3-fluorophenyl,4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl,4-bromophenyl, 2,3-dichlorophenyl, 2,4-dichlorophenyl,3,4-dichlorophenyl, 2-hydroxyphenyl, 3-hydroxyphenyl, 4-hydroxyphenyl,2-hydroxy-3-chlorophenyl, 2,6-dichlorophenyl, 2-hydroxy-5-chlorophenyl,2-hydroxy-2,5-dichlorophenyl, 2-hydroxy-3-bromophenyl,2-hydroxy-2,5-dibromophenyl, 4-hydroxy-3,5-dichlorophenyl,4-hydroxy-3,5-dibromophenyl, 2-hydroxy-3-methoxyphenyl,2-hydroxy-4-methoxyphenyl, 2-hydroxy-5-methoxyphenyl,3-methoxy-4-hydroxyphenyl, 4-hydroxy-3-methoxyphenyl, 2-methylphenyl,3-methylphenyl, 4-methylphenyl, 2,4-dimethylphenyl, 2,5 -dimethylphenyl,2,6-dimethylphenyl, 4-iso-propylphenyl, 4-tert-butylphenyl,4-sec-butylphenyl, 2-trifluoromethylphenyl, 3-trifluoromethylphenyl,4-trifluoromethylphenyl, 4-nitrophenyl, 2-hydroxy-3-nitrophenyl,2-hydroxy-5-nitrophenyl, 2-methoxyphenyl, 3-methoxyphenyl,4-methoxyphenyl, 4-ethoxyphenyl, 4-butoxyphenyl, 2,3-dimethoxyphenyl,2,4-dimethoxyphenyl, 2,5-dimethoxyphenyl, 3,4-dimethoxyphenyl,3,5-dimethoxyphenyl, 2,3,4-trimethoxyphenyl, 3,4,5-trimethoxyphenyl,2-fluorobenzyl, 3-fluorobenzyl, 4-fluorobenzyl, 2-chlorobenzyl,3-chlorobenzyl, 4-chlorobenzyl, 4-bromobenzyl, 2,4-dichlorobenzyl,2,6-dichlorobenzyl, 3,4-dichlorobenzyl, 4-nitrobenzyl, 2-methylbenzyl,3-methylbenzyl, 4-methylbenzyl, 2,4-dimethylbenzyl, 3,4-dimethylbenzyl,2,5-dimethylbenzyl, 4-iso-propylbenzyl, 4-sec-butylbenzyl,4-tert-butylbenzyl, 4-methoxybenzyl, 4-carboxyethylbenzyl,2-trifluoromethylbenzyl, 3-trifluoromethylbenzyl,4-trifluoromethylbenzyl, 2-thienyl, 3-thienyl, 2-furanyl, 3-furanyl,3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 2-thiazolyl, 2-thienylmethyl,5-chloro-2-thienyl, 5-chloro-2-thienylmethyl, 5-bromo-2-thienyl,5-chloro-3-thienyl, 5-bromo-3-thienyl, 5-methyl-2-thienyl,5-methyl-2-thienylmethyl, 2-furanylmethyl, 5-methyl-2-furanyl,5-methyl-2-furanylmethyl, 5-nitro-2-furanyl, 5-nitro-2-thienyl,3-isoxazolylmethyl, 4-isoxazolylmethyl, 5-isoxazolylmethyl, 2-pyridinyl,3-pyridinyl, 4-pyridinyl, 2-pyridinylmethyl, 3-pyridinylmethyl,4-pyridinylmethyl.

Furthermore, R⁴, together with R⁵ and the C atom whose substituents theyare, are also N-methyl-piperidinylene, N-methylpyrrolidinylene,tetrahydropyranylidene, tetrahydrofuranylidene, hexahydrooxazinylidene,hexahydrothiazinylidene or dithianylidene radicals.

The novel compounds can be prepared by reacting

a) hydrazines of the formula II ##STR5## with an oxalylhydroxamic esterof the formula III

    R--O--NH--CO--COOR.sup.6                                   (III)

where R, , R¹, R², R³ and R⁶ have the abovementioned meanings, or

b) an oxalyl hydrazide-hydroxamic acid ester of the formula IV ##STR6##with an aldehyde or ketone of the formula V ##STR7## where R, R¹, R⁴ andR⁵ have the abovementioned meanings, if appropriate in the presence of asolvent or diluent or an inorganic or organic base or an inorganic ororganic acid or a reaction accelerator or mixtures thereof.

Useful solvents for process variant a) are, for example,halohydrocarbons, in particular chlorohydrocarbons, e.g.1,1,2,2-tetrachloroethylene, or 1,1,2,2-tetrachloroethane,dichloropropane, methylene chloride, dichlorobutane, 1,1,1- or1,1,2-trichloroethane, trichloroethylene, o-, m-, or p-difluorobenzene,1,2-dichloroethane, 1,1-dichloroethane, 1,2-cis-dichloroethylene,chlorobenzene, fluorobenzene, bromobenzene, iodobenzene, o-, m- orp-dichlorobenzene, o-, p- or m-dibromobenzene, o-, m-, orp-chlorotoluene; ethers, e.g. ethyl propyl ether, methyl tert-butylether, n-butyl ethyl ether, di-n-butyl ether diisobutyl ether, diisoamylether, diisopropyl ether, anisole, phenetole, cyclohexyl methyl ether,diethyl ether, ethylene glycol dimethyl ether, tetrahydrofuran, dioxane,thioanisole; alcohols such as methanol, ethanol, propanol, isopropanol,n-butanol, isobutanol, tert-butanol, ethylene glycol and propanediols;nitriles such as acetonitrile, butyronitrile, isobutyronitrile,benzonitrile, m-chlorobenzonitrile; aliphatic or cycloaliphatichydrocarbons, e.g. heptane,- pinane, nonane, o-, m- or p-cymene,gasoline fractions within a boiling range from 70° to 190° C.,cyclohexane, methylcyclohexane, decalin, petroleum ether, hexane,ligroin, 2,2,4-trimethylpentane, 2,2,3-trimethylpentane,2,3,3-trimethylpentane, octane; esters e.g. ethyl acetate, acetoaceticester, isobutyl acetate; amides, e.g. formamide, methylformamide,dimethylformamide, and, if appropriate, also water and appropriatemixtures. The compounds of the formula I can also be used in excess assolvents. Expediently, the solvent is used in an amount from 100 to2000% by weight, preferably from 200 to 700% by weight, based onstarting substance III.

Suitable bases are, for example, potassium hydroxide, sodium hydroxide,potassium carbonate, sodium carbonate, lithium hydroxide, lithiumcarbonate, sodium bicarbonate, potassium bicarbonate, calcium hydroxide,calcium oxide, barium oxide, magnesium hydroxide, magnesium oxide,barium hydroxide, calcium carbonate, magnesium carbonate, magnesiumbicarbonate, magnesium acetate, zinc hydroxide, zinc oxide, zinccarbonate, zinc bicarbonate, zinc acetate, sodium formate, sodiumacetate, trimethylamine, triethylamine, tripropylamine,triisopropylamine, tributylamine, triisobutylamine, tri-sec-butylamine,tri-tert-butylamine, tribenzylamine, tricyclohexylamine, triamylamine,trihexylamine, N,N-dimethylaniline, N,N-diethylaniline,N,N-dipropylaniline, N,N-dimethyltoluidine, N,N-diethyltoluidine,N,N-dipropyltoluidine, N,N-dimethyl-4-aminopyridine,N,N-di-ethyl-4-aminopyridine, N,N-di-propyl-4-aminopyridine,N,N-dipropyl-4-aminopyridine, N-methylpyrolidine, N-ethylpyrrolidine,N-methylpiperidine, N-ethylpiperidine, N-methyl-pyrrolidine,N-ethyl-pyrrolidine, N-methylimidazole, N-ethylimidazole,N-methylmorpholine, N-ethylmorpholine, N-methylhexamethylenimine,N-ethylhexamethylenimine, pyridine, quinoline, alpha-picoline,beta-picoline, isoquinoline, pyrimidine, acridine, N,N,N',N'-tetramethylethylenediamine, N,N,N',N'-tetraethylethylenediamine,quinoxaline, N-propyldiisopropylamine, N,N-dimethylcyclohexylamine,2,6-lutidine, 2,4-lutidine and triethylenediamine.

Expediently, the base is used in stoichiometric amounts, in an excess ora deficit of in each case up to 20 mol %, based on the startingsubstance III.

It may additionally be useful to carry out the reaction in the presenceof a catalyst.

Suitable reaction accelerators are preferably 4-dimethylaminopyridineand 4-pyrrolidinopyridine (J. Cossy et al., Synthesis, (1989) 753f).

Starting substances of the formula III are disclosed in DE 4 022 265.

For process variant b), the reaction in general takes place attemperatures from -20° to 100° C., preferably from 15° to 80° C.

Useful solvents are, for example, those mentioned above in process a).The following are particularly suitable: acetic acid, ethyl acetate,methylene chloride, toluene, chlorobenzene, tetrahydrofuran, dioxane,methanol, ethanol, n-propanol, iso-propanol, n-butanol, iso-butanol andtert-butanol or mixtures thereof.

Suitable bases in this process in addition to the abovementioned arepotassium acetate and sodium acetate.

Apart from the compounds mentioned in the preparation examples, thefollowing oxalylhydrazide-hydroxamic acid derivatives of the generalformula I may specifically be mentioned:

                                      TABLE 1                                     __________________________________________________________________________    R            R.sup.1      R.sup.2        R.sup.3                              __________________________________________________________________________    H            H            H              H                                    CH.sub.3     H            H              H                                    CH.sub.3     CH.sub.3     H              H                                    CH.sub.3     CH.sub.3     CH.sub.3       H                                    CH.sub.3     H            CH.sub.3       CH.sub.3                             CH.sub.3     C.sub.2 H.sub.5                                                                            H              H                                    CH.sub.3     n-C.sub.3 H.sub.7                                                                          H              H                                    CH.sub.3     iso-C.sub.3 H.sub.7                                                                        H              H                                    CH.sub.3     H            C(CH.sub.3)    H                                    CH.sub.3     n-C.sub.4 H.sub.9                                                                          H              H                                    CH.sub.3     iso-C.sub.4 H.sub.9                                                                        H              H                                    CH.sub.3     n-C.sub.5 H.sub.11                                                                         H              H                                    CH.sub.3     iso-C.sub.5 H.sub.11                                                                       H              H                                    CH.sub.3     n-C.sub.6 H.sub.13                                                                         H              H                                    CH.sub.3     n-C.sub.8 H.sub.17                                                                         H              H                                    CH.sub.3     n-C.sub.10 H.sub.21                                                                        H              H                                    CH.sub.3     cyclopropyl  H              H                                    CH.sub.3     cyclopentyl  H              H                                    CH.sub.3     cyclohexyl   H              H                                    CH.sub.3     4-methylcyclo-                                                                             H              H                                                 hexyl                                                            CH.sub.3     cyclohexyl-  H              H                                                 methyl                                                           CH.sub.3     cycloheptyl  H              H                                    CH.sub.3     CH.sub.2 CH.sub.2 Cl                                                                       H              H                                    CH.sub.3     CH.sub.2 CH.sub.2 CH.sub.2 Cl                                                              H              H                                    CH.sub.3     (CH.sub.2).sub.4 Cl                                                                        H              H                                    CH.sub. 3    (CH.sub.2).sub.5 Cl                                                                        H              H                                    CH.sub.3     CH.sub.2 CF.sub.3                                                                          H              H                                    CH.sub.3     (CH.sub.2).sub.5 Br                                                                        H              H                                    CH.sub.3     CH.sub.2 CH.sub.2 OCH.sub.3                                                                H              H                                    CH.sub.3     (CH.sub.2).sub.3 OCH.sub.3                                                                 H              H                                    CH.sub.3     (CH.sub.2).sub.2 OC.sub.2 H.sub.5                                                          H              H                                    CH.sub.3     (CH.sub.2).sub.3 OC.sub.2 H.sub.5                                                          H              H                                    CH.sub.3     (CH.sub.2).sub.4 OCH.sub.3                                                                 H              H                                    CH.sub.3     CH.sub.2 CHCH.sub.2                                                                        H              H                                    CH.sub.3     CH.sub.2 CHCHCH.sub.3                                                                      H              H                                    CH.sub.3     CH.sub.2 CHCH(CH.sub.3).sub.2                                                              H              H                                    CH.sub.3     CH.sub.2 CHCHC.sub.2 H.sub.5                                                               H              H                                    CH.sub.3     CH.sub.2 CHCHC.sub.3 H.sub.7                                                               H              H                                    CH.sub.3     CH.sub.2 C(Cl)CH.sub.2                                                                     H              H                                    CH.sub.3     CH.sub.2 C(Br)CH.sub.2                                                                     H              H                                    CH.sub.3     CH.sub.2 CHCHCl                                                                            H              H                                    CH.sub.3     CH.sub.2 CHCHBr                                                                            H              H                                    CH.sub.3     H            C.sub.6 H.sub.5                                                                              H                                    CH.sub.3     H            C.sub.6 H.sub.5                                                                              CH.sub.3                             CH.sub.3     H            C.sub.6 H.sub.4 -4F                                                                          H                                    CH.sub.3     H            C.sub.6 H.sub.4 -4Cl                                                                         H                                    CH.sub.3     H            C.sub.6 H.sub.4 -2Cl                                                                         H                                    CH.sub.3     H            C.sub.6 H.sub.4 -4Br                                                                         H                                    CH.sub.3     H            C.sub.6 H.sub.4 -2CH.sub.3                                                                   H                                    CH.sub.3     H            C.sub.6 H.sub.4 -3CH.sub.3                                                                   H                                    CH.sub.3     H            C.sub.6 H.sub.4 -4CH.sub.3                                                                   H                                    CH.sub.3     H            C.sub.6 H.sub.4 -4CF.sub.3                                                                   H                                    CH.sub.3     H            C.sub.6 H.sub.4 -4NO.sub.2                                                                   H                                    CH.sub.3     H            C.sub.6 H.sub.4 -4OCH.sub.3                                                                  H                                    CH.sub.3     H            C.sub.6 H.sub.4 -4C(CH.sub.3).sub.3                                                          H                                    CH.sub.3     H            C.sub.6 H.sub.4 -4(OC.sub.2 H.sub.5)                                                         H                                    CH.sub.3     H            C.sub.6 H.sub.4 -4-N(CH.sub.3).sub.2                                                         H                                    CH.sub.3     H            C.sub.6 H.sub.4 -4-CONH.sub.2                                                                H                                    CH.sub.3     H            C.sub.6 H.sub.3 -2,4Cl.sub.2                                                                 H                                    CH.sub.3     H            C.sub.6 H.sub.3 -3,4Cl.sub.2                                                                 H                                    __________________________________________________________________________                              R.sup.2 + R.sup.3                                   __________________________________________________________________________    CH.sub.3     H            CHCH.sub.3                                          CH.sub.3     H            CHC.sub.2 H.sub.5                                   CH.sub.3     H            CHC.sub.3 H.sub.7 -n                                CH.sub.3     H            CHC.sub.3 H.sub.7 -iso                              CH.sub.3     H            CHC.sub.4 H.sub.9 -n                                CH.sub.3     H            CHC.sub.4 H.sub.9 -iso                              CH.sub.3     H            CHC.sub.4 H.sub.9 -tert                             CH.sub.3     H            CHC.sub.5 H.sub.11 -n                               CH.sub.3     H            CHC.sub.5 H.sub.11 -iso                             CH.sub.3     H            CHC.sub.6 H.sub.13 -n                               CH.sub.3     H            CHC.sub.7 H.sub.15 -n                               CH.sub.3     H            CHC.sub.8 H.sub.17 -n                               CH.sub.3     H            CHC.sub.9 H.sub.19 -n                               CH.sub.3     H            C(CH.sub.3).sub.2                                   CH.sub.3     H            C(CH.sub.3)C.sub.2 H.sub.5                          CH.sub.3     H            C(CH.sub.3)C.sub.3 H.sub.7 -n                       CH.sub.3     H            C(C.sub.2 H.sub.5).sub.2                            CH.sub.3     H            C(C.sub.3 H.sub.7).sub.2                            CH.sub.3     H            C(CH.sub.3)C.sub.4 H.sub.9 -n                       CH.sub.3     H            C(CH.sub.3)C.sub.4 H.sub.9 -iso                     CH.sub.3     H            C(CH.sub.3)C.sub.4 H.sub.9 -tert                    CH.sub.3     H            C(CH.sub.3)C.sub.5 H.sub.11 -n                      CH.sub.3     H            C(CH.sub.3)C.sub.6 H.sub.13 -n                      CH.sub.3     H            C(CH.sub.3)C.sub.7 H.sub.15 -n                      CH.sub.3     H            C(CH.sub.3)C.sub.8 H.sub.17 -n                      CH.sub.3     H            C(C.sub.4 H.sub.9)C.sub.6 H.sub.13 -n               CH.sub.3     H                                                                                           ##STR8##                                           CH.sub.3     H                                                                                           ##STR9##                                           CH.sub.3     H                                                                                           ##STR10##                                          CH.sub.3     H                                                                                           ##STR11##                                          CH.sub.3     H                                                                                           ##STR12##                                          CH.sub.3     H                                                                                           ##STR13##                                          CH.sub.3     H                                                                                           ##STR14##                                          CH.sub.3     H                                                                                           ##STR15##                                          CH.sub.3     H                                                                                           ##STR16##                                          CH.sub.3     H                                                                                           ##STR17##                                          CH.sub.3     H                                                                                           ##STR18##                                          CH.sub.3     H                                                                                           ##STR19##                                          CH.sub.3     H            CHCHCH.sub.2                                        CH.sub.3     H            CHCHCHCH.sub.3                                      CH.sub.3     H            CHCHC(CH.sub.3).sub.2                               CH.sub.3     H            CHC.sub.6 H.sub.5                                   CH.sub.3     H            CHCH.sub.2 C.sub.6 H.sub.5                          CH.sub.3     H            CHCH.sub.2 CH.sub.2 C.sub.6 H.sub.5                 CH.sub.3     H            CHCH(CH.sub.3)CH.sub.2 C.sub.6 H.sub.5              CH.sub.3     H            CHCHCHC.sub.6 H.sub.5                               CH.sub.3     H            CHC.sub.6 H.sub.4 -2F                               CH.sub.3     H            CHC.sub.6 H.sub.4 -3F                               CH.sub.3     H            CHC.sub.6 H.sub.4 -4F                               CH.sub.3     H            CHC.sub.6 H.sub.4 -2Cl                              CH.sub.3     H            CHC.sub.6 H.sub.4 -3Cl                              CH.sub.3     H            CHC.sub.6 H.sub.4 -4Cl                              CH.sub.3     H            CHC.sub.6 H.sub.3 -2OH-5Cl                          CH.sub.3     H            CHC.sub.6 H.sub.3 -2OH-3Cl                          CH.sub.3     H            CHC.sub.6 H.sub.2 -2OH-3,5Cl.sub.2                  CH.sub.3     H            CHC.sub.6 H.sub.4 -2OH                              CH.sub.3     H            CHC.sub.6 H.sub.4 -3OH                              CH.sub.3     H            CHC.sub.6 H.sub.4 -4OH                              CH.sub.3     H            CHC.sub.6 H.sub.4 -4Br                              CH.sub.3     H            CHC.sub.6 H.sub.3 -2OH-3Br                          CH.sub.3     H            CHC.sub.6 H.sub.3 -2OH-5Br                          CH.sub.3     H            CHC.sub.6 H.sub.2 -2OH-3,5Br.sub.2                  CH.sub.3     H            CHC.sub.6 HH.sub.3 -3Br-4OH                         CH.sub.3     H            CHC.sub.6 H.sub.3 -2,4-Cl.sub.2                     CH.sub.3     H            CHC.sub.6 H.sub.3 -3,4-Cl.sub.2                     CH.sub.3     H            CHC.sub.6 H.sub.4 -4CH.sub.3                        CH.sub.3     H            CHC.sub.6 H.sub.4 -4C.sub.3 H.sub.7 -iso            CH.sub.3     H            CHC.sub.6 H.sub.4 -4C.sub.4 H.sub.9 -tert           CH.sub.3     H            CHC.sub.6 H.sub.4 -4-C.sub.6 H.sub.13 -n            CH.sub.3     H            CHC.sub.6 H.sub.4 -2OCH.sub.3                       CH.sub.3     H            CHC.sub.6 H.sub.4 -3OCH.sub.3                       CH.sub.3     H            CHC.sub.6 H.sub.4 -4OCH.sub.3                       CH.sub.3     H            CHC.sub.6 H.sub.3 -2,4(OCH.sub.3).sub.2             CH.sub.3     H            CHC.sub.6 H.sub.3 -2,5(OCH.sub.3).sub.2             CH.sub.3     H            CHC.sub.6 H.sub.3 -3,4(OCH.sub.3).sub.2             CH.sub.3     H            CHC.sub.6 H.sub.3 -2,3(OCH.sub.3).sub.2             CH.sub.3     H            CHC.sub.6 H.sub.3 -3OH-4OCH.sub.3                   CH.sub.3     H            CHC.sub.6 H.sub.4 -4CF.sub.3                        CH.sub.3     H            CHC.sub.6 H.sub.4 -4NO.sub.2                        CH.sub.3     H            CHC.sub.6 H.sub.3 -2OH-5NO.sub.2                    CH.sub.3     H            CHC.sub.6 H.sub.4 -4-COOC.sub.2 H.sub.5             CH.sub.3     H            CHC.sub.6 H.sub.4 -4-CONH.sub.2                     CH.sub.3     H            CHC.sub.6 H.sub.4 -4-N(CH.sub.3).sub.2              CH.sub.3     H            CH-(thienyl-2)                                      CH.sub.3     H            CH-(thienyl-3)                                      CH.sub.3     H            CH-(5-chlorothienyl-2)                              CH.sub.3     H            CH-(5-bromothienyl-2)                               CH.sub.3     H            CH-(5-chlorothienyl-3)                              CH.sub.3     H            CH-(5-bromothienyl-3)                               CH.sub.3     H            CH-(5-methylthienyl-2)                              CH.sub.3     H            CH-(5-methylthienyl-3)                              CH.sub.3     H            CH-(furanyl-2)                                      CH.sub.3     H            CH-(5-methylfuranyl-2)                              CH.sub.3     H            CH-(pyridinyl-2)                                    CH.sub.3     H            CH-(pyridinyl-3)                                    CH.sub.3     H            CH-(pyridinyl-4)                                    CH.sub.3     H             CH-(isoxazolyl-3)                                  CH.sub.3     H            CH-(isoxazolyl-4)                                   CH.sub.3     H            CH-(isoxazolyl-5)                                   CH.sub.3     H            CH-(5-methylisoxazolyl-3)                           __________________________________________________________________________                              R.sup.2        R.sup.3                              __________________________________________________________________________    CH.sub.3     CH.sub.2 C.sub.6 H.sub.5                                                                   H              H                                    CH.sub.3     CH.sub.2 CH.sub.2C.sub.6 H.sub.5                                                           H              H                                    CH.sub.3     (CH.sub.3).sub.3C.sub.6 H.sub.5                                                            H              H                                    CH.sub.3     CH.sub.2 C.sub.6 H.sub.5 -4F                                                               H              H                                    CH.sub.3     CH.sub.2 C.sub.6 H.sub.4 -2F                                                               H              H                                    CH.sub.3     CH.sub.2 C.sub.6 H.sub.4 -2Cl                                                              H              H                                    CH.sub.3     CH.sub.2 C.sub.6 H.sub.4 -4Cl                                                              H              H                                    CH.sub.3     CH.sub.2 C.sub.6 H.sub.4 -4CH.sub.3                                                        H              H                                    CH.sub.3     CH.sub.2 C.sub.6 H.sub.4 -4OCH.sub.3                                                       H              H                                    CH.sub.3     CH.sub.2 C.sub.6 H.sub.4 -4C(CH.sub.3).sub.3                                               H              H                                    CH.sub.3     CH.sub.2 C.sub.6 H.sub.4 -4OC.sub.2 H.sub.5                                                H              H                                    CH.sub.3     CH.sub.2 C.sub.6 H.sub.4 -4OC.sub.3 H.sub.7                                                H              H                                    CH.sub.3     CH.sub.2 C.sub.6 H.sub.4 -4CF.sub. 3                                                       H              H                                    CH.sub.3     CH.sub.2 C.sub.6 H.sub.3 -2,4-Cl.sub.2                                                     H              H                                    C.sub.2 H.sub.5                                                                            H            H              H                                    C.sub.2 H.sub.5                                                                            CH.sub.3     H              H                                    C.sub.2 H.sub.5                                                                            CH.sub.3     CH.sub.3       H                                    C.sub.2 H.sub.5                                                                            H            CH.sub.3       CH.sub.3                             C.sub.2 H.sub.5                                                                            C.sub.2 H.sub.5                                                                            H              H                                    C.sub.2 H.sub.5                                                                            iso-C.sub.3 H.sub.7                                                                        H              H                                    C.sub.2 H.sub.5                                                                            n-C.sub.3 H.sub.7                                                                          H              H                                    C.sub.2 H.sub.5                                                                            H            C(CH.sub.3).sub.3                                                                            H                                    __________________________________________________________________________                              R.sup.2 + R.sup.3                                   __________________________________________________________________________    C.sub.2 H.sub.5                                                                            H            CHC.sub.4 H.sub.9 -n                                C.sub.2 H.sub.5                                                                            H            CHC.sub.5 H.sub.11 -n                               C.sub.2 H.sub.5                                                                            H            CHC.sub.9 H.sub.19 -n                               C.sub.2 H.sub.5                                                                            H            CHC.sub.6 H.sub.5                                   C.sub.2 H.sub.5                                                                            H            CHC.sub.6 H.sub.4 -2OH                              C.sub.2 H.sub.5                                                                            H            CHC.sub.6 H.sub.3 -2OH-3Cl                          C.sub.2 H.sub.5                                                                            H            CHC.sub.6 H.sub.3 -2OH-5Cl                          __________________________________________________________________________                              R.sup.2         R.sup.3                             __________________________________________________________________________    C.sub.2 H.sub.5                                                                            H            CHC.sub.6 H.sub.2 -2OH-3,5Cl.sub.2                  C.sub.2 H.sub.5                                                                            H            CHC.sub.6 H.sub.4 -4Cl                                                                        m.p.                                C.sub.2 H.sub.5                                                                            H            CHCHCHC.sub.6 H.sub.5                                                                         330° C.                      C.sub.2 H.sub.5                                                                            H            CHCHCHC.sub.6 H.sub.4 -4OCH.sub.3                   C.sub.2 H.sub.5                                                                            H                                                                                           ##STR20##                                          C.sub.2 H.sub.5                                                                            H                                                                                           ##STR21##                                          C.sub.2 H.sub.5                                                                            H                                                                                           ##STR22##                                          C.sub.2 H.sub.5                                                                            H                                                                                           ##STR23##                                          C.sub.2 H.sub.5                                                                            H            C.sub.6 H.sub.5 H                                   C.sub.2 H.sub.5                                                                            H            C.sub.6 H.sub.5 CH.sub.3                            C.sub.3 H.sub.7 -n                                                                         H            H               H                                   C.sub.3 H.sub.7 -n                                                                         CH.sub.3     H               H                                   C.sub.3 H.sub.7 -n                                                                         CH.sub.3     CH.sub.3        H                                   C.sub.3 H.sub.7 -n                                                                         H            CH.sub.3        CH.sub.3                            C.sub.3 H.sub.7 -n                                                                         iso-C.sub.3 H.sub.7                                                                        H               H                                   C.sub.3 H.sub.7 -n                                                                         H            C.sub.6 H.sub.5 H                                   C.sub.3 H.sub.7 -n                                                                         H            C.sub.6 H.sub.5 CH.sub.3                            __________________________________________________________________________                              R.sup.2 + R.sup.3                                   __________________________________________________________________________    C.sub.3 H.sub.7 -n                                                                         H                                                                                           ##STR24##                                          C.sub.3 H.sub.7 -n                                                                         H                                                                                           ##STR25##                                          C.sub.3 H.sub.7 -n                                                                         H                                                                                           ##STR26##                                          C.sub.3 H.sub.7 -n                                                                         H                                                                                           ##STR27##                                          C.sub.3 H.sub.7 -n                                                                         H                                                                                           ##STR28##                                          C.sub.3 H.sub.7 -iso                                                                       H            H              H                                    C.sub.3 H.sub.7 -n                                                                         H            CHC.sub.9 H.sub.19 -n                               C.sub.3 H.sub.7 -n                                                                         H            CHC.sub.10 H.sub.21 -n                              C.sub.3 H.sub.7 -n                                                                         H            CHC.sub.13 H.sub.27 -n                              C.sub.3 H.sub.7 -n                                                                         H            CHC.sub.6 H.sub.5                                   C.sub.3 H.sub.7 -n                                                                         H            CHC.sub.6 H.sub.4 -2OH                              C.sub.3 H.sub.7 -n                                                                         H            CHC.sub.6 H.sub.4 -3OH                              C.sub.3 H.sub.7 -n                                                                         H            CHC.sub.6 H.sub.4 -4OH                              C.sub.3 H.sub.7 -n                                                                         H            CHC.sub.6 H.sub.3 -2OH-3Cl                          C.sub.3 H.sub.7 -n                                                                         H            CH C.sub.6 H.sub.3 -2OH-5Cl                         C.sub.3 H.sub.7 -n                                                                         H            CHC.sub.6 H.sub.2 -2OH-3,5Cl.sub.2                  C.sub.3 H.sub.7 -n                                                                         H            CHC CH                                              C.sub.3 H.sub.7 -n                                                                         H            CHC CCH.sub.3                                       __________________________________________________________________________                              R.sup.2          R.sup.3                            __________________________________________________________________________    C.sub.4 H.sub.9 -n                                                                         H            H                H                                  C.sub.4 H.sub.9 -n                                                                         CH.sub.3     H                H                                  C.sub.4 H.sub.9 -n                                                                         CH.sub.3     CH.sub.3         H                                  C.sub.4 H.sub.9 -n                                                                         H            CH.sub.3         CH.sub.3                           C.sub.4 H.sub.9 -n                                                                         iso-C.sub.3 H.sub.7                                                                        H                H                                  C.sub.4 H.sub.9 -n                                                                         iso-C.sub.3 H.sub.7                                                                        CHC.sub.6 H.sub.4 -2OH                              C.sub.4 H.sub.9 -n                                                                         iso-C.sub.3 H.sub.7                                                                        CHCHCHC.sub.6 H.sub.4 -2OCH.sub.3                   C.sub.4 H.sub.9 -n                                                                         H            C.sub.6 H.sub.5  H                                  C.sub.4 H.sub.9 -n                                                                         H            CH.sub.2 C.sub.6 H.sub.5                                                                       H                                  __________________________________________________________________________                              R.sup.2 + R.sup.3                                   __________________________________________________________________________    C.sub.4 H.sub.9 -n                                                                         H            CHC.sub.15 H.sub.31 -n                              C.sub.4 H.sub.9 -n                                                                         H            CHC.sub.17 H.sub.35 -n                              C.sub.4 H.sub.9 -n                                                                         H            CHC.sub.6 H.sub.3 -2OH-3Cl                          C.sub.4 H.sub.9 -n                                                                         H            CHC.sub.6 H.sub.3 -2OH-5Cl                          C.sub.4 H.sub.9 -n                                                                         H                                                                                           ##STR29##                                          C.sub.4 H.sub.9 -n                                                                         H                                                                                           ##STR30##                                          C.sub.4 H.sub.9 -n                                                                         H                                                                                           ##STR31##                                          __________________________________________________________________________                              R.sup.2        R.sup.3                              __________________________________________________________________________    C.sub.4 H.sub.9 -iso                                                                       H            H              H                                    C.sub.4 H.sub.9 -iso                                                                       CH.sub.3     H              H                                    C.sub.4 H.sub.9 -iso                                                                       H            CH.sub.3       H                                    C.sub.4 H.sub.9 -iso                                                                       CH.sub.3     CH.sub.3       H                                    C.sub.4 H.sub.9 -iso                                                                       H            CH.sub.3       CH.sub.3                             C.sub.4 H.sub.9 -iso                                                                       C.sub.2 H.sub.5                                                                            H              H                                    C.sub.4 H.sub.9 -iso                                                                       C.sub.3 H.sub.7 -iso                                                                       H              H                                    C.sub.4 H.sub.9 -iso                                                                       H            C(CH.sub.3).sub.3                                                                            H                                    C.sub.4 H.sub.9 -iso                                                                       H            C.sub.6 H.sub.5                                                                              H                                    C.sub.4 H.sub.9 -iso                                                                       H            C.sub.6 H.sub.5                                                                              CH.sub.3                             C.sub.4 H.sub.9 -iso                                                                       H            C.sub.6 H.sub.4 -4F                                                                          H                                    C.sub.4 H.sub.9 -iso                                                                       H            C.sub.6 H.sub.4 -4Cl                                                                         H                                    C.sub.4 H.sub.9 -iso                                                                       H            C.sub.6 H.sub.4 -4CH.sub.3                                                                   H                                    C.sub.4 H.sub.9 -iso                                                                       H            C.sub.6 H.sub.4 -4N(CH.sub.3).sub.2                                                          H                                    C.sub.4 H.sub.9 -iso                                                                       H            CHC.sub.3 H.sub.7 -n                                C.sub.4 H.sub.9 -iso                                                                       H            CHC.sub.4 H.sub.9 -iso                              C.sub.4 H.sub.9 -iso                                                                       H            CHC.sub.5 H.sub.11 -n                               C.sub.4 H.sub.9 -iso                                                                       H            CHC.sub.9 H.sub.19 -n                               C.sub.4 H.sub.9 -iso                                                                       H            C(CH.sub.3)C.sub.3 H.sub.7                          __________________________________________________________________________                              R.sup.2 + R.sup.3                                   __________________________________________________________________________    C.sub.4 H.sub.9 -iso                                                                       H                                                                                           ##STR32##                                          C.sub.4 H.sub.9 -iso                                                                       H                                                                                           ##STR33##                                          C.sub.4 H.sub.9 -iso                                                                       H                                                                                           ##STR34##                                          C.sub.4 H.sub.9 -iso                                                                       H                                                                                           ##STR35##                                          C.sub.4 H.sub.9 -iso                                                                       H                                                                                           ##STR36##                                          C.sub.4 H.sub.9 -iso                                                                       H            CHCHCHCH.sub.3                                      C.sub.4 H.sub.9 -iso                                                                       H            CHCHC(CH.sub.3).sub.2                               C.sub.4 H.sub.9 -iso                                                                       H            CHC.sub.6 H.sub.5                                   C.sub.4 H.sub.9 -iso                                                                       H            CHCH.sub.2 C.sub.6 H.sub.5                          C.sub.4 H.sub.9 -iso                                                                       H            CHCH.sub.2 CH.sub.2 C.sub.6 H.sub.5                 C.sub.4 H.sub.9 -iso                                                                       H            CHCHCHC.sub.6 H.sub.5                               C.sub.4 H.sub.9 -iso                                                                       H            CHC.sub.6 H.sub.4 -4F                               C.sub.4 H.sub.9 -iso                                                                       H            CHC.sub.6 H.sub.4 -4Cl                              C.sub.4 H.sub.9 -iso                                                                       H            CHC.sub.6 H.sub.4 -CF.sub.3                         C.sub.4 H.sub.9 -iso                                                                       H            CHC.sub.6 H.sub.4 -CH.sub.3                         C.sub.4 H.sub.9 -iso                                                                       H            CHC.sub.6 H.sub.4 -4OCH.sub.3                       C.sub.4 H.sub.9 -iso                                                                       H            CHC.sub.6 H.sub.4 -2OH                              C.sub.4 H.sub.9 -iso                                                                       H            CHC.sub.6 H.sub.3 -2OH-3Cl                          C.sub.4 H.sub.9 -iso                                                                       H            CHC.sub.6 H.sub.3 -2OH-5Cl                          C.sub.4 H.sub.9 -iso                                                                       H            CH-(3-pyridinyl)                                    C.sub.4 H.sub.9 -iso                                                                       H            CHCHCHC.sub.6 H.sub.4 4Cl                           __________________________________________________________________________                              R.sup.2        R.sup.3                              __________________________________________________________________________    C.sub.4 H.sub.9 -iso                                                                       CH.sub.2 C.sub.6 H.sub.5                                                                   H              H                                    C.sub.5 H.sub.11 -n                                                                        H            H              H                                    C.sub.4 H.sub.9 -iso                                                                       H            C.sub.6 H.sub.4 -4C(CH.sub.3).sub.3                                                          H                                    C.sub.4 H.sub.9 -iso                                                                       H            C.sub.6 H.sub.4 -4OCH.sub.3                                                                  H                                    C.sub.4 H.sub.9 -iso                                                                       H            C.sub.6 H.sub.4 -4CF.sub.3                                                                   H                                    C.sub.4 H.sub.9 -iso                                                                       H            C.sub.6 H.sub.4 -4NO.sub.2                                                                   H                                    C.sub.4 H.sub.9 -iso                                                                       C.sub.6 H.sub.4 -4OC.sub.2 H.sub.5                                                         H                                                   C.sub.5 H.sub.11 -n                                                                        CH.sub.3     H              H                                    C.sub.5 H.sub.11 -n                                                                        CH.sub.3     CH.sub.3       H                                    C.sub.5 H.sub.11 -n                                                                        iso-C.sub.3 H.sub.7                                                                        H              H                                    C.sub.5 H.sub.11 -n                                                                        H            CH.sub.3       CH.sub.3                             C.sub.6 H.sub.13 -n                                                                        H            H              H                                    C.sub.6 H.sub.13 -n                                                                        CH.sub.3     H              H                                    C.sub.6 H.sub.13 -n                                                                        H            CH.sub.3       CH.sub.3                             C.sub.6 H.sub.13 -n                                                                        H            C.sub.6 H.sub.5                                                                              H                                    C.sub.8 H.sub.17 -n                                                                        H            H              H                                    C.sub.8 H.sub.17 -n                                                                        CH.sub.3     H              H                                    C.sub.8 H.sub.17 -n                                                                        iso-C.sub.3 H.sub.7                                                                        H              H                                    C.sub.8 H.sub.17 -n                                                                        H            C.sub.6 H.sub.5                                                                              H                                    C.sub.10 H.sub.21 -n                                                                       H            H              H                                    C.sub.10 H.sub.21 -n                                                                       CH.sub.3     H              H                                    C.sub.10 H.sub.21 -n                                                                       iso-C.sub.3 H.sub.7                                                                        H              H                                    C.sub.10 H.sub.21 -n                                                                       H            CH.sub.3       CH.sub.3                             C.sub.12 H.sub.25 -n                                                                       H            H              H                                    C.sub.12 H.sub.25 -n                                                                       CH.sub.3     H              H                                    C.sub.12 H.sub.25 -n                                                                       H            C.sub.6 H.sub.5                                                                              H                                    C.sub.14 H.sub.29 -n                                                                       H            H              H                                    C.sub.14 H.sub.29 -n                                                                       iso-C.sub.3 H.sub.7                                                                        H              H                                    C.sub.18 H.sub.37 -n                                                                       H            H              H                                    C.sub.20 H.sub.41 -n                                                                       H            H              H                                    ClCH.sub.2 CH.sub.2                                                                        H            H              H                                    Cl(CH.sub.2).sub.3                                                                         H            H              H                                    Cl(CH.sub.2).sub.4                                                                         H            H              H                                    Cl(CH.sub.2).sub.6                                                                         H            H              H                                    Cl(CH.sub.2).sub.8                                                                         H            H              H                                    Br(CH.sub.2).sub. 4                                                                        H            H              H                                    CF.sub.3 CH.sub.2                                                                          H            H              H                                    CH.sub.2 CHCH.sub.2                                                                        H            H              H                                    CH.sub.2 CHCH.sub.2                                                                        H            CH.sub.3       CH.sub.3                             CH.sub.2 CHCH.sub.2                                                                        iso-C.sub.3 H.sub.7                                                                        H              H                                    CHCHCH.sub.2 H            C.sub.6 H.sub.5                                                                              H                                    CH.sub.2 CHCHCH.sub.3                                                                      H            H              H                                    CH.sub.2 CHC(CH.sub.3).sub.2                                                               H            H              H                                    CH.sub.2 CH.sub.2 CHCH.sub.2                                                               H            H              H                                    CH.sub.2 CHCHC.sub.2 H.sub.5                                                               H            H              H                                    CH.sub.2 CHCHC.sub.3 H.sub.7 -n                                                            H            H              H                                    CH.sub.2 CHCHC.sub.4 H.sub.9 -n                                                            H            H              H                                    CH.sub.2 C(Cl)CH.sub.2                                                                     H            H              H                                    CH.sub.2 CHCHCL                                                                            H            H              H                                    CH.sub.2 C(Br)CH.sub.2                                                                     H            H              H                                    CH.sub.2 CHC(Cl).sub.2                                                                     H            H              H                                    CH.sub.2 (Cl)CCl.sub.2                                                                     H            H              H                                    CH.sub.2 CH.sub.2 OCH.sub.3                                                                H            H              H                                    (CH.sub.2).sub.3 OCH.sub.3                                                                 H            H              H                                    (CH.sub.2).sub.2 OC.sub.2 H.sub.5                                                          H            H              H                                    (CH.sub.2).sub.2 OC.sub.3 H.sub.7 -n                                                       H            H              H                                    (CH.sub.2).sub.3 OC.sub.2 H.sub.5                                                          H            H              H                                    (CH.sub.2).sub.3 OC.sub.3 H.sub.7 -n                                                       H            H              H                                    (CH.sub.3).sub.3 OC.sub.4 H.sub.9 -n                                                       H            H              H                                    cyclopropyl  H            H              H                                    cyclobutyl   H            H              H                                    cyclopentyl  H            H              H                                    cyclopentylmethyl                                                                          H            H              H                                    cyclohexyl   H            H              H                                    4-methylcyclohexyl                                                                         H            H              H                                    cyclohexylmethyl                                                                           H            H              H                                    cycloheptyl  H            H              H                                    CH.sub.2 C.sub.6 H.sub.5                                                                   H            H              H                                    CH.sub.2 CH.sub.2 C.sub.6 H.sub.5                                                          H            H              H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.5                                                           H            H              H                                    CH.sub.2 CH(CH.sub.3)CH.sub.2 C.sub.6 H.sub.5                                              H            H              H                                    CH.sub.2 CHCHC.sub.6 H.sub.5                                                               H            H              H                                    CH.sub.2 C.sub.6 H.sub.4 -2F                                                               H            H              H                                    CH.sub.2 C.sub.6 H.sub.4 -4F                                                               H            H              H                                    CH.sub.2 C.sub.6 H.sub.4 -2Cl                                                              H            H              H                                    CH.sub.2 C.sub.6 H.sub.4 -3Cl                                                              H            H              H                                    CH.sub.2 C.sub.6 H.sub.4 -4Cl                                                              H            H              H                                    CH.sub.2 C.sub.6 H.sub.4 -4CH.sub.3                                                        H            H              H                                    CH.sub.2 C.sub.6 H.sub.4 -2OCH.sub.3                                                       H            H              H                                    CH.sub.2 C.sub.6 H.sub.4 -3OCH.sub.3                                                       H            H              H                                    CH.sub.2 C.sub.6 H.sub.4 -4OCH.sub.3                                                       H            H              H                                    CH.sub.2 C.sub.6 H.sub.4 -4OC.sub.2 H.sub.5                                                H            H              H                                    CH.sub.2 C.sub.6 H.sub.4 -4CF.sub.3                                                        H            H              H                                    CH.sub.2 C.sub.6 H.sub.3 -2,4-Cl.sub.2                                                     H            H              H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 4Cl                                                       H            H              H                                    __________________________________________________________________________

How the novel active ingredients of the formula I are manufactured andused will be apparent from the following examples.

Manufacturing examples Example 1

1-(Ethoxyamino)-2-(hydrazino)-ethane-1,2-dione

A solution of 234 g (1.59 mol) of methyl (ethoxyamino)-oxoacetate in 450ml of ethanol was added to a solution of 92.8 g (1.855 mol) of hydrazinehydrate in 300 ml of ethanol and the mixture was stirred for 2 hours at65° C. The mixture was cooled to +10° C., the precipitate was suctionfiltered, washed with a small amount of cold ethanol, and dried. Therewas obtained 150 g (64.2% of theory) of1-(ethoxyamino)-2-(hydrazino)-ethane-1,2-dione as white crystals of m.p.182° C.

Example 2

1-(Ethoxyamino)-2-[(4-chlorophenylmethylene)-hydrazino]-ethane-1,2-dione

9 g (0.07 mol) of 4-chlorobenzaldehyde was added to a solution of 10.3 g(0.07 mol) of 1-(ethoxyamino)-2-(hydrazino)-ethane-1,2-dione (Example 1)in 100 ml of acetic acid, and the mixture was stirred for 30 minutes at40° C. The precipitate was suction filtered, washed with ether anddried. There was obtained 12.2 g (65% of theory) of1-(ethoxyamino)-2-[4-chlorophenylmethylene)-hydrazino]-ethane-1,2-dioneas white crystals of m.p. 330° C. (decomp.).

The compounds of the formula I listed in Table 2 below were obtainedanalogously to the manufacturing examples and in accordance with thegeneral manufacturing details:

                                      TABLE 2                                     __________________________________________________________________________    No.                                                                              R           R.sup.1                                                                            R.sup.2      R.sup.3                                                                          m.p. (°C.)                         __________________________________________________________________________     3 C.sub.2 H.sub.5                                                                           H                                                                                   ##STR37##      130-131                                    4 C.sub.2 H.sub.5                                                                           H                                                                                   ##STR38##      123-125                                    5 C.sub.2 H.sub.5                                                                           H                                                                                   ##STR39##      110-112                                    6 C.sub.2 H.sub.5                                                                           H                                                                                   ##STR40##      120-122                                    7 CH.sub.2 CHCH.sub.2                                                                       H    H            H  185-186                                    8 CH.sub.2 CHCH.sub.2                                                                       H    CHC.sub.6 H.sub.4 -4Cl                                                                        300 (decomp.)                              9 CH.sub.2 C(Br)CH.sub.2                                                                    H    H            H  130-131                                   10 C.sub.3 H.sub.7 -n                                                                        H    H            H  159-161                                   11 C.sub.3 H.sub.7 -n                                                                        H    CHC.sub.6 H.sub.4 -4Cl                                                                        258-259                                   12 C.sub.3 H.sub.7 -n                                                                        H    CHC.sub.6 H.sub.4 -4OCH.sub.3                                                                 199-201                                   13 C.sub.3 H.sub.7 -n                                                                        H    CHC.sub.6 H.sub.3 -3,4(OCH.sub.3).sub.2                                                       209-211                                   14 C.sub.3 H.sub.7 -iso                                                                      H    H            H  142-145                                   15 C.sub.3 H.sub.7 -iso                                                                      H    CHC.sub.6 H.sub.4 -4OCH.sub.3                                                                 243-245                                   16 C.sub.3 H.sub.7 -iso                                                                      H    CHC.sub.6 H.sub.3 -3,4(OCH.sub.3).sub.2                                                       198-201                                   17 C.sub.3 H.sub.7 -iso                                                                      H    CHC.sub.6 H.sub.2 -3,4,5(OCH.sub.3).sub.3                                                     235-238                                   18 C.sub.3 H.sub.7 -iso                                                                      H                                                                                   ##STR41##      158-159                                   19 C.sub.3 H.sub.7 -iso                                                                      H                                                                                   ##STR42##      138-140                                   20 C.sub.3 H.sub.7 -iso                                                                      H                                                                                   ##STR43##      117-118                                   21 C.sub.3 H.sub.7 -iso                                                                      H                                                                                   ##STR44##      120-121                                   22 CH.sub.2 C(CH.sub.3)CH.sub.2                                                              H    H            H  142-144                                   23 CH.sub.2 C(CH.sub.3)CH.sub.2                                                              H    CHC.sub.6 H.sub.4 -4Cl                                                                        277-280                                   24 CH.sub.2 C(CH.sub.3)CH.sub.2                                                              H    CHC.sub.6 H.sub.4 -4CF.sub.3                                                                  310 (decomp.)                             25 CH.sub.2 C(CH.sub.3)CH.sub.2                                                              H    CHC.sub.6 H.sub.4 -4OCH.sub.3                                                                 300 (decomp.)                             26 CH.sub.2 C(CH.sub.3)CH.sub.2                                                              H    CHC.sub.6 H.sub.3 -3,4(OCH.sub.3).sub.2                                                       205-208                                   27 C.sub.4 H.sub.9 -n                                                                        H    H            H  150-151                                   28 C.sub.4 H.sub.9 -n                                                                        H    CHC.sub.6 H.sub.4 -4OCH.sub.3                                                                 217-220                                   29 C.sub.4 H.sub.9 -n                                                                        H    CHC.sub.6 H.sub.3 -3,4(OCH.sub.3).sub.2                                                       217-219                                   30 C.sub.4 H.sub.9 -n                                                                        H    CHC.sub.6 H.sub.3 -3,4Cl.sub.2                                                                203-205                                   31 C.sub.4 H.sub.9 -iso                                                                      H    H            H  151-153                                   32 C.sub.4 H.sub.9 -iso                                                                      CH.sub.3                                                                           H            H  130-131                                   33 C.sub.4 H.sub.9 -iso                                                                      H    CH.sub.3     CH.sub.3                                                                         107-111                                   34 C.sub.4 H.sub.9 -iso                                                                      C.sub.3 H.sub.7 -iso                                                               H            H  135-136                                   35 C.sub.4 H.sub.9 -iso                                                                      H    CHC.sub.6 H.sub.5                                                                             143-146                                   36 C.sub.4 H.sub.9 -iso                                                                      H    CH C.sub.6 H.sub.4 -2OH                                                                       218-220                                   37 C.sub.4 H.sub.9 -iso                                                                      H    CHC.sub.6 H.sub.4 -4C(CH.sub.3).sub.3                                                         275-277                                   38 C.sub.4 H.sub.9 -iso                                                                      H    CHC.sub.6 H.sub.4 -4OCH.sub.3                                                                 230                                       39 C.sub.4 H.sub.9 -iso                                                                      H    CHC.sub.6 H.sub.3 -3,4(OCH.sub.3).sub.2                                                       212-215                                   40 C.sub.4 H.sub.9 -iso                                                                      H    CHC.sub.6 H.sub.3 -2OH-5Cl                                                                    238-240                                   41 C.sub.4 H.sub.9 -iso                                                                      H                                                                                   ##STR45##      153-155                                   42 C.sub.4 H.sub.9 -iso                                                                      H                                                                                   ##STR46##      122-125                                   43 C.sub.4 H.sub.9 -iso                                                                      H                                                                                   ##STR47##      112-115                                   44 C.sub.4 H.sub.9 -iso                                                                      CH.sub.3                                                                            ##STR48##      157-158                                   45 C.sub.4 H.sub.9 -iso                                                                      H                                                                                   ##STR49##      105-108                                   46 C.sub.4 H.sub.9 -iso                                                                      H                                                                                   ##STR50##      112-114                                   47 C.sub.4 H.sub.9 -iso                                                                      H                                                                                   ##STR51##      154-156                                   48 CH.sub.2 C.sub.6 H.sub.5                                                                  H    H            H  156-158                                   49 CH.sub.2 C.sub.6 H.sub.5                                                                  H    CHC.sub.6 H.sub.4 -4Cl                                                                        274-278                                   50 CH.sub.2 C.sub.6 H.sub.5                                                                  H    CHC.sub.6 H.sub.4 -4OCH.sub.3                                                                 249-250                                   51 CH.sub.2 C.sub.6 H.sub.5                                                                  H    CHC.sub.6 H.sub.3 -3,4(OCH.sub.3).sub.2                                                       240-241                                   52 C.sub.2 H.sub.5                                                                           H                                                                                   ##STR52##      resin                                     53 C.sub.3 H.sub.7 -iso                                                                      H                                                                                   ##STR53##      117-120                                   __________________________________________________________________________

In general terms, the novel compounds are extremely effective on a broadspectrum of phytopathogenic fungi, in particular those from the classconsisting of the Ascomycetes and Basidiomycetes. Some of them have asystemic action and can be used as foliar and soil fungicides.

The fungicidal compounds are of particular interest for controlling alarge number of fungi in various crops or their seeds, especially wheat,rye, barley, oats, rice, Indian corn, lawns, cotton, soybeans, coffee,sugar cane, fruit and ornamentals in horticulture and viticulture, andin vegetables such as cucumbers, beans and cucurbits.

The novel compounds are particularly useful for controlling thefollowing plant diseases:

Erysiphe graminis in cereals,

Erysiphe cichoracearum and Sphaerotheca fuliginea in cucurbits,

Podosphaera leucotricha in apples,

Uncinula necator in vines,

Puccinia species in cereals,

Rhizoctonia solani in cotton,

Ustilago species in cereals and sugar cane,

Venturia inaequalis (scab) in apples,

Helminthosporium species in cereals,

Septoria nodorum in wheat,

Botrytis cinerea (gray mold) in strawberries and grapes,

Cercospora arachidicola in groundnuts,

Pseudocercosporella herpotrichoides in wheat and barley,

Pyricularia oryzae in rice,

Phytophthora infestans in potatoes and tomatoes,

Fusarium and Verticillium species in various plants,

Plasmopara viticola in grapes,

Alternaria species in fruit and vegetables.

The compounds are applied by spraying or dusting the plants with theactive ingredients, or treating the seeds of the plants with the activeingredients. They may be applied before or after infection of the plantsor seeds by the fungi.

The novel substances can be converted into conventional formulationssuch as solutions, emulsions, suspensions, dusts, powders, pastes andgranules. The application forms depend entirely on the purposes forwhich they are intended; they should at all events ensure a fine anduniform distribution of the active ingredient. The formulations areproduced in known manner, for example by extending the active ingredientwith solvents and/or carriers, with or without the use of emulsifiersand dispersants; if water is used as solvent, it is also possible toemploy other organic solvents as auxiliary solvents. Suitableauxiliaries for this purpose are solvents such as aromatics (e.g.,xylene), chlorinated aromatics (e.g., chlorobenzenes), paraffins (e.g.,crude oil fractions), alcohols (e.g., methanol, butanol), ketones (e.g.,cyclohexanone), amines (e.g., ethanolamine, dimethylformamide), andwater; carriers such as ground natural minerals (e.g., kaolins,aluminas, talc and chalk) and ground synthetic minerals (e.g., highlydisperse silica and silicates); emulsifiers such as nonionic and anionicemulsifiers (e.g., polyoxyethylene fatty alcohol ethers, alkylsulfonates and aryl sulfonates); and dispersants such as lignin-sulfitewaste liquors and methylcellulose.

The fungicidal agents generally contain from 0.1 to 95, and preferablyfrom 0.5 to 90, wt % of active ingredient. The application rates arefrom 0.02 to 3 kg or more of active ingredient per hectare, depending onthe type of effect desired. The novel compounds may also be used forprotecting materials, e.g., on Paecilomyces variotii.

When the active ingredients are used for treating seed, rates of from0.001 to 50, and preferably from 0.01 to 10, g of active ingredient perkg of seed are generally required.

The agents and the ready-to-use formulations prepared from them, such assolutions, emulsions, suspensions, powders, dusts, pastes and granules,are applied in conventional manner, for example by spraying, atomizing,dusting, scattering, dressing or watering.

Examples of formulations are given below.

I. A solution of 90 parts by weight of the compound of Example 1 and 10parts by weight of N-methyl-u-pyrrolidone, which is suitable forapplication in the form of very fine drops.

II. A mixture of 20 parts by weight of the compound of Example 2, 80parts by weight of xylene, 10 parts by weight of the adduct of 8 to 10moles of ethylene oxide and 1 mole of oleic acid-N-monoethanolamide, 5parts by weight of the calcium salt of dodecylbenzenesulfonic acid, and5 parts by weight of the adduct of 40 moles of ethylene oxide and 1 moleof castor oil. By finely dispersing the mixture in water, an aqueousdispersion is obtained.

III. An aqueous dispersion of 20 parts by weight of compound no. 3 fromTable 2, 40 parts by weight of cyclohexanone, 30 parts by weight ofisobutanol, 20 parts by weight of the adduct of 40 moles of ethyleneoxide and 1 mole of castor oil. By pouring the mixture into water andfinely distributing it therein, and aqueous dispersion is obtained.

IV. An aqueous dispersion of 20 parts by weight of compound no. 4 fromTable 2, 25 parts by weight of cyclohexanol, 65 parts by weight of amineral oil fraction having a boiling point between 210° and 280° C.,and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1mole of castor oil. By pouring the mixture into water and finelydistributing it therein, and aqueous dispersion is obtained.

V. A hammer-milled mixture of 80 parts by weight of compound no. 5 fromTable 2, 3 parts by weight of the sodium salt ofdiisobutylnaphthalene-α-sulfonic acid, 10 parts by weight of the sodiumsalt of a lignin-sulfonic acid obtained from a sulfite waste liquor, and7 parts by weight of powdered silica gel. By finely dispersing themixture in water, a spray liquor is obtained.

VI. An intimate mixture of 3 parts by weight of compound no. 6 fromTable 2 and 97 parts by weight of particulate kaolin. The dust contains3 wt % of the active ingredient.

VII. An intimate mixture of 30 parts by weight of compound no. 7 fromTable 2, 92 parts by weight of powdered silica gel and 8 parts by weightof paraffin oil sprayed onto the surface of this silica gel. Thisformulation of the active ingredient exhibits good adherence.

VIII. A stable aqueous dispersion of 40 parts by weight of compound no.8 from Table 2, 10 parts of the sodium salt of a phenolsulfonicacid-urea-formaldehyde condensate, 2 parts of silica gel and 48 parts ofwater, which dispersion can be further diluted.

IX. A stable oily dispersion of 20 parts by weight of compound no. 9from Table 2, 2 parts by weight of the calcium salt ofdodecylbenzenesulfonic acid, 8 parts by weight of a fatty alcoholpolyglycol ether, 2 parts by weight of the sodium salt of aphenolsulfonic acid-urea-formaldehyde condensate and 68 parts by weightof a paraffinic mineral oil.

In these application forms, the agents according to the invention mayalso be present together with other active ingredients, for exampleherbicides, insecticides, growth regulators, and fungicides, and mayfurthermore be mixed and applied together with fertilizers. Admixturewith other fungicides frequently results in a greater fungicidal actionspectrum.

The prior art active ingredient used in the following comparativeexperiments was Tridemorph (A)--disclosed in U.S. Pat. No. 3,686,394.

Use Example 1 Action on Fusarium culmorum in wheat

True leaves of pot-grown wheat seedlings of the "Kanzler" variety weresprayed to runoff with aqueous spray liquors containing (dry basis) 80%of active ingredient and 20% of emulsifier. The next day they wereinoculated with a spore suspension of Fusarium culmorum and placed in aclimatic chamber of high humidity (>90%) at 22°-24° C. The extent offungus spread was assessed visually after 6 days.

The results of this experiment show that compounds nos. 9, 10, 14, 27,31, 35, 41, 45, 46 and 47, when applied as spray liquors containing 500ppm of active ingredient, have an excellent fungicidal action (10%attack).

Use Example 2 Action on Botrytis cinerea

Paprika seedlings of the "Neusiedler Ideal Elite" variety were sprayed,after 4 to 5 leaves were well developed, to runoff with aqueoussuspensions containing (dry basis) 80% of active ingredient and 20% ofemulsifier. After the sprayed-on layer had dried, the plants weresprinkled with a conidial suspension of the fungus Botrytis cinerea, andplaced at 22° to 24° C. in a chamber of high humidity. After 5 days, thedisease had spread to such a great extent on the untreated plants thatthe necroses covered the major portion of the leaves.

The results of this experiment show that compounds nos. 7, 22, 24, 26,31, 42, 45 and 46, when applied as spray liquors containing 500 ppm ofactive ingredient, have a better fungicidal action (10% attack) thanprior art active ingredient A (60% attack).

We claim
 1. An oxalyl hydrazide-hydroxamic acid derivative of thegeneral formula I ##STR54## where the substituents have the followingmeanings: R, R¹, R² and R³ independently of one another arehydrogen, C₁-C₂₀ -alkyl, C₃ -C₁₈ -alkenyl or C₃ -C₈ -alkynyl, where these radicalscan carry one to five halogen atoms or one to three C₁ -C₄ -alkoxygroups, if appropriate together with the halogen atoms; monocyclic orpolycyclic C₃ -C₁₀ -cycloalkyl or C₃ -C₁₀ -cycloalkylmethyl, where theserings can carry one to three C₁ -C₄ -alkyl groups or a cyclohexyl ring;monocyclic or polycyclic C₅ -C₁₀ -cycloalkenyl or C₅ -C₁₀-cycloalkenylmethyl, where these rings can carry one to three C₁ -C₄-alkyl groups or a cyclohexyl ring; phenyl, phenyl-C₁ -C₄ -alkyl,phenyl-C₂ -C₆ -alkenyl, where the phenyl radicals can carry one to fivehalogen atoms or one to three of the following groups, if appropriatetogether with the halogen atoms: hydroxyl, nitro, C₁ -C₄ -alkyl, C₁ -C₄-haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy or amines, or R² togetherwith R³ is the group ##STR55## where R⁴ and R⁵ are one of the radicalsR, R¹, R² or R³ or R⁴, together with R⁵ and the C atom whosesubstituents they are, are monocyclic or polycyclic C₃ -C₁₀ -cycloalkyl,where these rings can carry one to three C₁ -C₄ -alkyl groups or aphenyl ring, wherein R, R¹, R² and R³ are not simultaneously hydrogen.2. A method for controlling fungi, which comprises treating the fungi orthe materials, plants, seeds or the soil threatened by fungal attackwith a fungicidally effective amount of an oxalyl hydrazide-hydroxamicacid derivative of the formula of claim
 1. 3. A fungicide, containing aninert carrier and a fungicidally effective amount of anoxalyl-hydrazidehydroxamic acid derivative of the formula I of claim 1.4. A compound of the formula I as claimed in claim 1, where R is ethyl,and R¹, R² and R³ are hydrogen.
 5. A compound of the formula I asclaimed in claim 1, where R is ethyl, R¹ is hydrogen, and R² and R³together are the group ##STR56## wherein R⁴ and R⁵ together with thecarbon atom to which they are attached are 4-chlorophenylmethylene.
 6. Acompound of the formula I as claimed in claim 1, where R is ethyl, R¹ ishydrogen, and R² and R³ together are the group ##STR57## wherein R⁴ andR⁵ together with the carbon atom to which they are attached arecyclopentylene.
 7. A compound of the formula I as claimed in claim 1,where R is ethyl, R¹ is hydrogen, and R² and R³ together are the group##STR58## wherein R⁴ and R⁵ together with the carbon atom to which theyare attached are cyclohexylene.
 8. A compound of the formula I asclaimed in claim 1, where R is ethyl, R¹ is hydrogen, and R² and R³together are the group ##STR59## wherein R⁴ and R⁵ together with thecarbon atom to which they are attached are 3-methylcyclohexylene.
 9. Theacid of claim 1, wherein R¹, R² and R³ independently of one anotherarehydrogen, C₁ -C₂₀ -alkyl, C₃ -C₁₈ -alkenyl or C₃ -C₈ -alkynyl, wherethese radicals are unsubstituted or substituted with 1-5 halogen atomsor 1-3 C₁ -C₄ alkoxy groups; monocyclic or polycyclic C₃ -C₁₀-cycloalkyl or C₃ -C₁₀ -cycloalkylmethyl, where these rings areunsubstituted or substituted with 1-3 C₁ -C₄ -alkyl groups or acyclohexyl ring; monocyclic or polycyclic C₅ -C₁₀ -cycloalkenyl or C₅-C₁₀ -cycloalkenylmethyl, where these rings are unsubstituted orsubstituted with 1-3 C₁ -C₄ -alkyl groups or a cyclohexyl ring; phenyl,phenyl-C₁ -C₄ -alkyl, phenyl-C₂ -C₆ -alkenyl, where the phenyl ring ofthese groups is unsubstituted or substituted with 1-5 halogen atoms or1-3 groups selected from the group consisting of hydroxyl, nitro, C₁ -C₄-alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy or amines.10. The acid of claim 9, wherein R¹, R² and R³ independently of oneanother arehydrogen, C₁ -C₂₀ -alkyl, C₃ -C₁₈ -alkenyl or C₃ -C₈-alkynyl, where these radicals are unsubstituted or substituted with 1-5halogen atoms or 1-3 C₁ -C₄ alkoxy groups; monocyclic or polycyclic C₃-C₁₀ -cycloalkyl or C₃ -C₁₀ -cycloalkylmethyl, where these rings areunsubstituted or substituted with 1-3 C₁ -C₄ -alkyl groups or acyclohexyl ring; monocyclic or polycyclic C₅ -C₁₀ -cycloalkenyl or C₅-C₁₀ -cycloalkenylmethyl, where these rings are unsubstituted orsubstituted with 1-3 C₁ -C₄ -alkyl groups or a cyclohexyl ring.
 11. Theacid of claim 10, wherein R¹, R² and R³ independently of one anotherarehydrogen, C₁ -C₂₀ -alkyl, C₃ -C₁₈ -alkenyl or C₃ -C₈ -alkynyl, wherethese radicals are unsubstituted or substituted with 1-5 halogen atomsor 1-3 C₁ -C₄ alkoxy groups.
 12. A compound of the formula I as claimedin claim 1, wherein R is isobutyl, R¹ is hydrogen, R² is hydrogen and R³is hydrogen.
 13. An oxalyl hydrazide-hydroxamic acid derivative of thegeneral formula I ##STR60## where the substituents have the followingmeanings: R is C₁ -C₂₀ -alkyl, C₃ -C₁₈ -alkenyl or C₃ -C₈ -alkynyl,where these radicals can carry one to five halogen atoms or one thethree C₁ -C₄ -alkoxy groups, if appropriate together with the halogenatoms;monocyclic or polycyclic C₃ -C₁₀ -cycloalkyl or C₃ -C₁₀-cycloalkylmethyl, where these rings can carry one to three C₁ -C₄-alkyl groups or a cyclohexyl ring; monocyclic or polycyclic C₅ -C₁₀-cycloalkenyl or C₅ -C₁₀ -cycloalkenylmethyl, where these rings cancarry one to three C₁ -C₄ -alkyl groups or a cyclohexyl ring; phenyl,phenyl-C₁ -C₄ -alkyl, phenyl-C₂ -C₆ -alkenyl, where the phenyl radicalscan carry one to five halogen atoms or one to three of the followinggroups, if appropriate together with the halogen atoms: hydroxyl, nitro,C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy C₁ -C₄ -haloalkoxy oramines, R¹, R² and R³ independently of one another are hydrogen, C₁ -C₂₀-alkyl, C₃ -C₁₈ -alkenyl or C₃ -C₈ -alkynyl, where these radicals cancarry one to five halogen atoms or one the three C₁ -C₄ -alkoxy groups,if appropriate together with the halogen atoms; monocyclic or polycyclicC₃ -C₁₀ -cycloalkyl or C₃ -C₁₀ -cycloalkylmethyl, where these rings cancarry one to three C₁ -C₄ -alkyl groups or a cyclohexyl ring; monocyclicor polycyclic C₅ -C₁₀ -cycloalkenyl or C₅ -C₁₀ -cycloalkenylmethyl,where these rings can carry one to three C₁ -C₄ -alkyl groups or acyclohexyl ring; phenyl, phenyl-C₁ -C₄ -alkyl, phenyl-C₂ -C₆ -alkenyl,where the phenyl radicals can carry one to five halogen atoms or one tothree of the following groups, if appropriate together with the halogenatoms: hydroxyl, nitro, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄-alkoxy, C₁ -C₄ -haloalkoxy or amines, or R² together with R³ is thegroup ##STR61## where R⁴ and R⁵ are one of the radicals R, R¹, R², or R³; or R⁴ together with R⁵ and the carbon atom whose substituents theyare, are monocyclic or polycyclic C₃ -C₁₀ -cycloalkyl, where these ringscan carry one to three C₁ -C₄ -alkyl groups or a phenyl ring.